Mid-October is about a month late. Lake Ontario boat clubs start hauling between Oct. 15-30, and supplies are going to dry up close to the water by then. If you are leaving via Oswego, check the end of season date for that transit, and work backwards. Remember you've got to factor in two half-days for hauling the mast down and up on that route.
We sail as late as mid-November (we were hauled privately last year), but we only cruise to mid-October away from Toronto. I would say that if you exited the Welland Canal into Lake Ontario by October 10, you would have plenty of time to get to NYC by Oct. 15., but as Cam said, you are going to have some crappy and possibly stormy weather going south to the Chesapeake in the following 10 days. The good news is that the October sailing on Lakes Erie and Ontario, while tending to be windy and sometimes cool, is frequently glorious and full of "single reef and a No. 3" reaching.
As for leaving from Lake Superior, I wouldn't be on that beast much after Sept. 15.